EP1432051A2 - Procédé de dopage d'un polymère - Google Patents
Procédé de dopage d'un polymère Download PDFInfo
- Publication number
- EP1432051A2 EP1432051A2 EP04075962A EP04075962A EP1432051A2 EP 1432051 A2 EP1432051 A2 EP 1432051A2 EP 04075962 A EP04075962 A EP 04075962A EP 04075962 A EP04075962 A EP 04075962A EP 1432051 A2 EP1432051 A2 EP 1432051A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- polymer
- dopant
- conjugated polymer
- precursor
- doping
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 102
- 238000000034 method Methods 0.000 title claims abstract description 52
- 239000002019 doping agent Substances 0.000 claims abstract description 83
- 229920000547 conjugated polymer Polymers 0.000 claims abstract description 73
- 239000002243 precursor Substances 0.000 claims abstract description 60
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims description 24
- -1 poly(fluorenes) Polymers 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 229920001577 copolymer Polymers 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000010408 film Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000004793 Polystyrene Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000001212 derivatisation Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 229920000867 polyelectrolyte Polymers 0.000 description 5
- 229920006254 polymer film Polymers 0.000 description 5
- 239000002861 polymer material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000000542 sulfonic acid group Chemical group 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000009102 absorption Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 3
- 229910006069 SO3H Inorganic materials 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- QLZHNIAADXEJJP-UHFFFAOYSA-L dioxido-oxo-phenyl-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000004803 parallel plate viscometry Methods 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- KGWYICAEPBCRBL-UHFFFAOYSA-N 1h-indene-1-carboxylic acid Chemical group C1=CC=C2C(C(=O)O)C=CC2=C1 KGWYICAEPBCRBL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910018828 PO3H2 Inorganic materials 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000005388 borosilicate glass Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000013043 chemical agent Substances 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 125000005520 diaryliodonium group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 125000005409 triarylsulfonium group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- YSWBUABBMRVQAC-UHFFFAOYSA-N (2-nitrophenyl)methanesulfonic acid Chemical group OS(=O)(=O)CC1=CC=CC=C1[N+]([O-])=O YSWBUABBMRVQAC-UHFFFAOYSA-N 0.000 description 1
- HXBMIQJOSHZCFX-UHFFFAOYSA-N 1-(bromomethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1CBr HXBMIQJOSHZCFX-UHFFFAOYSA-N 0.000 description 1
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 229910004354 OF 20 W Inorganic materials 0.000 description 1
- 241000702619 Porcine parvovirus Species 0.000 description 1
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000012682 cationic precursor Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000012955 diaryliodonium Substances 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- RSJLWBUYLGJOBD-UHFFFAOYSA-M diphenyliodanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[I+]C1=CC=CC=C1 RSJLWBUYLGJOBD-UHFFFAOYSA-M 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012465 retentate Substances 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical compound S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y20/00—Nanooptics, e.g. quantum optics or photonic crystals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
- G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
- G02B6/122—Basic optical elements, e.g. light-guiding paths
- G02B6/1221—Basic optical elements, e.g. light-guiding paths made from organic materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/114—Poly-phenylenevinylene; Derivatives thereof
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
- G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
- G02B2006/12035—Materials
- G02B2006/12069—Organic material
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
- G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
- G02B2006/12083—Constructional arrangements
- G02B2006/12104—Mirror; Reflectors or the like
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01S—DEVICES USING THE PROCESS OF LIGHT AMPLIFICATION BY STIMULATED EMISSION OF RADIATION [LASER] TO AMPLIFY OR GENERATE LIGHT; DEVICES USING STIMULATED EMISSION OF ELECTROMAGNETIC RADIATION IN WAVE RANGES OTHER THAN OPTICAL
- H01S3/00—Lasers, i.e. devices using stimulated emission of electromagnetic radiation in the infrared, visible or ultraviolet wave range
- H01S3/14—Lasers, i.e. devices using stimulated emission of electromagnetic radiation in the infrared, visible or ultraviolet wave range characterised by the material used as the active medium
- H01S3/16—Solid materials
- H01S3/168—Solid materials using an organic dye dispersed in a solid matrix
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01S—DEVICES USING THE PROCESS OF LIGHT AMPLIFICATION BY STIMULATED EMISSION OF RADIATION [LASER] TO AMPLIFY OR GENERATE LIGHT; DEVICES USING STIMULATED EMISSION OF ELECTROMAGNETIC RADIATION IN WAVE RANGES OTHER THAN OPTICAL
- H01S5/00—Semiconductor lasers
- H01S5/30—Structure or shape of the active region; Materials used for the active region
- H01S5/36—Structure or shape of the active region; Materials used for the active region comprising organic materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
- H10K50/852—Arrangements for extracting light from the devices comprising a resonant cavity structure, e.g. Bragg reflector pair
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08162762A EP1995800B1 (fr) | 1999-04-06 | 2000-04-05 | Procédé pour le dopage d'un polymère |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9907802 | 1999-04-06 | ||
GBGB9907802.4A GB9907802D0 (en) | 1998-07-14 | 1999-04-06 | Doping |
EP00919019A EP1166281B1 (fr) | 1999-04-06 | 2000-04-05 | Procede de dopage d'un polymere |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00919019A Division EP1166281B1 (fr) | 1999-04-06 | 2000-04-05 | Procede de dopage d'un polymere |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP08162762A Division EP1995800B1 (fr) | 1999-04-06 | 2000-04-05 | Procédé pour le dopage d'un polymère |
Publications (3)
Publication Number | Publication Date |
---|---|
EP1432051A2 true EP1432051A2 (fr) | 2004-06-23 |
EP1432051A3 EP1432051A3 (fr) | 2007-11-07 |
EP1432051B1 EP1432051B1 (fr) | 2008-10-08 |
Family
ID=10850999
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP08162762A Expired - Lifetime EP1995800B1 (fr) | 1999-04-06 | 2000-04-05 | Procédé pour le dopage d'un polymère |
EP00919019A Expired - Lifetime EP1166281B1 (fr) | 1999-04-06 | 2000-04-05 | Procede de dopage d'un polymere |
EP04075962A Expired - Lifetime EP1432051B1 (fr) | 1999-04-06 | 2000-04-05 | Procédé de dopage d'un polymère |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP08162762A Expired - Lifetime EP1995800B1 (fr) | 1999-04-06 | 2000-04-05 | Procédé pour le dopage d'un polymère |
EP00919019A Expired - Lifetime EP1166281B1 (fr) | 1999-04-06 | 2000-04-05 | Procede de dopage d'un polymere |
Country Status (10)
Country | Link |
---|---|
US (4) | US6835803B1 (fr) |
EP (3) | EP1995800B1 (fr) |
JP (2) | JP4486758B2 (fr) |
KR (2) | KR100667290B1 (fr) |
CN (2) | CN100412994C (fr) |
AT (3) | ATE270788T1 (fr) |
AU (1) | AU3977900A (fr) |
DE (3) | DE60012000T2 (fr) |
HK (1) | HK1046771B (fr) |
WO (1) | WO2000060612A1 (fr) |
Cited By (1)
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US9650245B2 (en) | 2002-08-09 | 2017-05-16 | Semiconductor Energy Laboratory Co., Ltd. | Organic electroluminescent device |
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CN100412994C (zh) * | 1999-04-06 | 2008-08-20 | 剑桥显示技术有限公司 | 掺杂聚合物的方法 |
AU4937300A (en) | 1999-06-09 | 2000-12-28 | Cambridge Display Technology Limited | Method of producing organic light-emissive devices |
EP1289342B1 (fr) * | 2001-09-04 | 2006-11-22 | Sony Deutschland GmbH | Mélanges de polymères alignés émetteurs de lumière, film polymèryque et dispositif utilisant ces mélanges |
SG111090A1 (en) * | 2002-10-25 | 2005-05-30 | Agency Science Tech & Res | Cationic water-soluble conjugated polymers and their precursors |
EP1441399A3 (fr) * | 2003-01-25 | 2009-07-01 | MERCK PATENT GmbH | Dopants polymères |
JP2004343051A (ja) | 2003-01-25 | 2004-12-02 | Merck Patent Gmbh | ポリマードーパント |
DE102004007399B4 (de) * | 2004-02-16 | 2007-12-27 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Polymersystem mit definiert einstellbarer Ladungsträgerbeweglichkeit und dessen Verwendung |
EP2325191A1 (fr) * | 2004-03-11 | 2011-05-25 | Mitsubishi Chemical Corporation | Composition pour une couche transportant des charges et pour un composé ionique, couche transportant des charges et composant électroluminescent organique utilisant celle-ci |
US6930322B1 (en) * | 2004-03-26 | 2005-08-16 | Matsushita Electric Industrial Co., Ltd. | Combination insulator and organic semiconductor formed from self-assembling block co-polymers |
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KR100715548B1 (ko) * | 2005-07-29 | 2007-05-07 | 광 석 서 | 부분 치환된 고분자 도판트를 사용하여 합성된 전도성고분자 |
CN101297415A (zh) * | 2005-08-01 | 2008-10-29 | 普莱克斯托尼克斯公司 | 导电聚合物的潜在掺杂 |
EP1919000A1 (fr) * | 2005-08-05 | 2008-05-07 | Matsushita Electric Industries Co., Ltd. | Dispositif électroluminescent à semi-conducteur |
US20070077452A1 (en) * | 2005-10-04 | 2007-04-05 | Jie Liu | Organic light emitting devices having latent activated layers and methods of fabricating the same |
US20070176167A1 (en) * | 2006-01-27 | 2007-08-02 | General Electric Company | Method of making organic light emitting devices |
EP2008318B1 (fr) * | 2006-03-21 | 2013-02-13 | Novaled AG | Procede de preparation de materiaux semiconducteurs organiques dopes |
GB0617723D0 (en) * | 2006-09-08 | 2006-10-18 | Cambridge Display Tech Ltd | Conductive polymer compositions in opto-electrical devices |
EP1912268B1 (fr) * | 2006-10-09 | 2020-01-01 | Novaled GmbH | Méthode de structuration spatiale de l'émission d'une OLED, dispositif organique électroluminescent obtenu par cette méthode, et son usage |
US20080145697A1 (en) * | 2006-12-13 | 2008-06-19 | General Electric Company | Opto-electronic devices containing sulfonated light-emitting copolymers |
DE102008046857A1 (de) | 2007-12-17 | 2009-06-18 | Osram Opto Semiconductors Gmbh | OLED für Betrieb mit Wechselspannung und Herstellungsverfahren |
EP2851383A1 (fr) | 2008-04-11 | 2015-03-25 | Solvay USA Inc. | Polymères conjugués dopés, dispositifs et procédés de fabrication des dispositifs |
JP2011525918A (ja) * | 2008-06-27 | 2011-09-29 | ユニバーサル ディスプレイ コーポレイション | 架橋可能なイオンドーパント |
JP2010212212A (ja) * | 2009-03-12 | 2010-09-24 | Sanyo Electric Co Ltd | 導電性高分子膜、導電性高分子材料、及び電子デバイス |
WO2012121417A1 (fr) * | 2011-03-09 | 2012-09-13 | Waseda University | Mélanges de polymère conducteur/polymère redox obtenus par polymérisation oxydative in situ, leurs procédés de préparation et application en tant que matériaux polymères électroactifs |
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EA028833B1 (ru) | 2014-09-30 | 2018-01-31 | Сикпа Холдинг Са | Жидкость, содержащая полимерный маркер, применение полимерного маркера в качестве инструмента аутентификации, а также способ и устройство для обнаружения полимерного маркера, растворенного в жидкости |
WO2016126209A1 (fr) * | 2015-02-03 | 2016-08-11 | National University Of Singapore | Matériaux polymériques conducteurs électriques à dopage de type p pour couches d'injection de trous et d'extraction de trous |
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WO2017097391A1 (fr) * | 2015-12-10 | 2017-06-15 | Merck Patent Gmbh | Formulations contenant des cétones comprenant des cycles non aromatiques |
WO2017136598A1 (fr) * | 2016-02-02 | 2017-08-10 | Polydrop, Llc | Films polymères conjugués transparents |
GB2551730A (en) * | 2016-06-28 | 2018-01-03 | Sumitomo Chemical Co | Method and composition |
US20180240565A1 (en) | 2017-02-17 | 2018-08-23 | Polydrop, Llc | Conductive polymer-matrix compositions and uses thereof |
NL2022110B1 (en) | 2018-11-30 | 2020-06-26 | Univ Delft Tech | Electrochemical doping of semiconductor materials |
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2000
- 2000-04-05 CN CNB008070512A patent/CN100412994C/zh not_active Expired - Lifetime
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- 2000-04-05 EP EP08162762A patent/EP1995800B1/fr not_active Expired - Lifetime
- 2000-04-05 WO PCT/GB2000/001288 patent/WO2000060612A1/fr active IP Right Grant
- 2000-04-05 KR KR1020067019695A patent/KR100667290B1/ko active IP Right Grant
- 2000-04-05 EP EP00919019A patent/EP1166281B1/fr not_active Expired - Lifetime
- 2000-04-05 US US09/958,257 patent/US6835803B1/en not_active Expired - Lifetime
- 2000-04-05 CN CN2008101356573A patent/CN101319045B/zh not_active Expired - Lifetime
- 2000-04-05 AT AT08162762T patent/ATE470958T1/de not_active IP Right Cessation
- 2000-04-05 DE DE60012000T patent/DE60012000T2/de not_active Expired - Lifetime
- 2000-04-05 DE DE60044543T patent/DE60044543D1/de not_active Expired - Lifetime
- 2000-04-05 EP EP04075962A patent/EP1432051B1/fr not_active Expired - Lifetime
- 2000-04-05 DE DE60040492T patent/DE60040492D1/de not_active Expired - Lifetime
- 2000-04-05 AU AU39779/00A patent/AU3977900A/en not_active Abandoned
- 2000-04-05 AT AT04075962T patent/ATE410791T1/de not_active IP Right Cessation
- 2000-04-05 KR KR1020017012766A patent/KR100674686B1/ko active IP Right Grant
- 2000-04-05 JP JP2000610019A patent/JP4486758B2/ja not_active Expired - Lifetime
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- 2002-11-14 HK HK02108243.6A patent/HK1046771B/zh not_active IP Right Cessation
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- 2004-04-07 US US10/819,622 patent/US7008999B2/en not_active Expired - Lifetime
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